1) FLATTERING A RASHA
QUESTION: The Gemara discusses at length the severity of the sin of "Chanufah," flattery. One who uses Chanufah will be punished with Galus in this world and will descend to Gehinom in the next. The Gemara says that one of the four groups of people who will not merit to greet the Shechinah is the group of those who use Chanufah.
Earlier (41b), however, Rebbi Yehudah bar Ma'arava (or, according to others, Rebbi Shimon ben Pazi) teaches that one is permitted to use Chanufah and flatter Resha'im in this world. If Chanufah is permitted, why is the punishment for it so severe?
ANSWERS:
(a) The simple answer is that one is permitted to flatter a Rasha only by emphasizing the good qualities which he actually possesses. One may not praise the evil that a Rasha does. The Chachamim were punished for using Chanufah with Agripas because they supported his wrongful ascension to the throne. Rebbi Shimon ben Pazi, on the other hand, permits calling a "Naval" (a vile person) a "Nadiv," generous, when that person gives money to Tzedakah, despite his evil traits. Reish Lakish derives that this form of Chanufah is permitted from the verse which relates that Yakov Avinu greeted Esav by declaring how honored he was to see that Esav no longer harbored ill feelings towards him.
RAV MOSHE FEINSTEIN zt'l takes this approach in practice (IGROS MOSHE OC 2:51). He points out that according to the way the Chachamim describe the prohibition of Chanufah, the prohibition applies only when one praises a Rasha for an evil deed and gives the impression that the evil deed is permitted.
(b) However, RABEINU YONAH (Sha'arei Teshuvah, Sha'ar 3:189) writes explicitly that even praising a Rasha for his positive traits and deeds while ignoring his evil traits and deeds is not permitted, since such praise causes other people to think that the Rasha did only good and no evil. He finds support for this in the verse in Mishlei (28:4) which states that those who desert the Torah are the ones who praise a Rasha (see also Sotah 42b, "Asur l'Saper b'Shivchan Shel Resha'im").
(It is possible that Rabeinu Yonah only prohibits praising a Rasha for the moral acts which he does when he normally acts unethically toward his fellow man. One who praises the person for matters of Bein Adam la'Chaveiro and ignores his negative aspects of Bein Adam la'Chaveiro appears as though he encourages the person's general conduct of Bein Adam la'Chaveiro and not just the specific good act which he did. If, however, the Rasha sins only Bein Adam la'Makom, one may praise him for his ethical conduct Bein Adam la'Chaveiro because such praise does not show an acceptance of the way he acts Bein Adam la'Makom. See Rabeinu Yonah there, 3:187.)
Rabeinu Yonah explains that the Gemara permits one to flatter a Rasha when the Rasha happens to be wealthy or powerful, and because of his wealth or power people normally honor him by showing him respect. Although it is clear to everyone that the reason one is showing respect for the person is because of his wealth or power, nevertheless if he is a Rasha it is not proper to show him respect but, on the contrary, one should try to lower his stature in the eyes of the people so that he should be motivated to repent. However, if there is a possibility that acting in such a way will cause one to suffer personal damage at the hands of the Rasha, one is permitted to act toward the wealthy Rasha in the same way in which he would act toward any other wealthy person.
If the Rasha is not wealthy or powerful, one may never praise him for any good deeds that he does.
2) SUMMARY: THE FOUR GROUPS THAT WILL NOT GREET THE SHECHINAH
The Gemara teaches that four groups of people will not merit to greet the Shechinah in the World to Come: Letzim (scoffers), Chanifim (flatterers), Shakranim (liars), and Mesaprei Lashon ha'Ra (slanderers). RABEINU YONAH (Sha'arei Teshuvah 3:172-231) discusses in detail the various aspects of these four groups, and he lists the different categories within each group. His words shed much light on the definitions of these groups. We will summarize here the different categories of each group, which Rabeinu Yonah lists in order of decreasing severity.
1. LETZANIM (five categories):
(a) A person who spreads false rumors about others in order to degrade them. (This constitutes Lashon ha'Ra as well.)
(b) One who degrades others because of what they lack.
(c) One who constantly scoffs at specific items or actions (because he thinks he is smarter than everyone else and knows better what course of action to take).
(d) One who wastes time with non-productive talk and activities (Bitul Torah).
(e) A joker who tries to attract attention by making jokes. (This manifestation of Letzanus often occurs as a result of inebriation.)
2. CHANIFIM (nine categories):
(a) One who sees his friend sin and encourages him, and tells his friend that that he did nothing wrong.
(b) One who sees his friend sin and compliments him for his good qualities and ignores his evil deeds (see previous Insight).
(c) One who sees his friend sin and compliments him in private, encouraging his friend to continue to sin but not encouraging others to follow his ways.
(d) One who sees another person sin and becomes friendly with him and joins his company of friends.
(e) One who praises his friends or relatives for good deeds that they did not actually perform, in order to enhance his relationship with them.
(f) One who sees someone sin and does not rebuke him when his rebuke would be effective.
(g) One who sees someone sin and does not rebuke him when he is in doubt whether or not his rebuke would be effective to stop the sinner from sinning.
(h) One is present when a person sins, and although he knows for certain that the sinner will not accept his rebuke, he does not even protest the action. Although he knows that his protest will not have an effect on the sinner, he must show others his disapproval of the act.
(i) One honors a sinner who happens to be wealthy or powerful, and honors him as he honors other wealthy or powerful people who are not sinners. (Chanufah in this case is permitted when there is a risk that the wealthy or powerful sinner will cause him to suffer damage if he does not give the Rasha the honor he thinks he deserves. See previous Insight.)
3. SHAKRANIM (9 categories):
(a) One who lies in order to steal from or abuse others, thereby transgressing the prohibitions of "Lo Sigzol" and "Lo Soneh."
(b) One who lies in order to present himself as someone's friend so that at some point in the future he will be able to steal from him or swindle him.
(c) One who lies in order to receive some future benefit that he would not have received otherwise.
(d) One who lies (even though he causes no harm) simply because he is accustomed to lying, or because he does not clarify the facts before he repeats them. (This is permitted "Mipnei ha'Shalom," for the sake of peace; see Insights to Yevamos 65b.)
(e) One who acts towards others differently than the way he feels inside, even though he does not openly lie.
(f) One who promises to give something to (or do something for) his friend and does not fulfill his promise. If he offers his friend something small or easy, even if he does not make a promise to give it he still must keep his word.
(g) One who tells others about the way he helped someone else, when he really did not help (Geneivas Da'as).
(h) One who praises himself, or accepts praise, for good traits that he does not possess.
(i) A person who occasionally lies regarding issues that in no way affect others, but merely because he derives benefit (such as attention) from his lies.
4. MESAPREI LASHON HA'RA (6 categories):
(a) A person who slanders someone else with a false claim (same as 1-a above).
(b) One who slanders others by telling the truth about what the other person's parents did or what the other person himself did before he repented, in order to cause others to lose esteem for him.
(c) One who informs his friend about the slander that someone else said about him (Rechilus).
(d) One who does something that causes others to suspect him of speaking Lashon ha'Ra. For example, he relates his friend's good deeds in the presence of his friend's enemy (Avak Lashon ha'Ra).
(e) One who speaks "Nivul Peh" -- immoral speech and expletives.
(f) One who constantly complains about others and judges them unfavorably (Nirgan).

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